Methyl iodide → 2-tert-Butyl-6-(3-tert-butyl-2-methoxy-5-methylbenzyl)-4-methylphenol

HRID 273760

Reaction equation

HRID 273760 reaction equation
[CH2:1]([C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:15]=1[OH:25])[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:3]=1[OH:13].[Cl-].[Ca+2].[Cl-].[CH3:29]I>CC(C)=O>[CH3:29][O:25][C:15]1[C:16]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][C:18]([CH3:20])=[CH:19][C:14]=1[CH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:3]=1[OH:13]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 83982,2'-Methylenebis(4-methyl-6-tert-butylphenol)HCID 5284359Calcium Chloride

Product 1

HCID 6012872-tert-Butyl-6-(3-tert-butyl-2-methoxy-5-methylbenzyl)-4-methylphenolYield 79.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

34 g of 2,2'-methylenebis(6-tert-butyl-4-methylphenol) was dissolved in 50 ml of acetone and 27.6 g of anhydrous calcium chloride was added to this solution. 15 g of methyl iodide was slowly added dropwise thereto while stirring under reflux. After stirring for 6 hours, the reaction mixture was cooled and solid matter was filtered off. The filtrate was poured into ice-water and the formed crystals were filtered off. The crystals were recrystallized from water-containing methanol to obtain 28.2 g of compound (59).

Workup

  1. temperatureunder reflux
  2. stirringAfter stirring for 6 hours
  3. temperaturethe reaction mixture was cooled
  4. filtrationsolid matter was filtered off
  5. additionThe filtrate was poured into ice-water
  6. filtrationthe formed crystals were filtered off
  7. customThe crystals were recrystallized from water-
  8. additioncontaining methanol

Sources & evidence

ORD record
ord-4a4456ca75d44a348bf0ad7d7e193af0
Source dataset
uspto-grants-1995_02
Patent number
US05387600

Linked notes

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